A Charmed Life

In some respects, I have led a charmed life. In 1955, shortly after starting my own organometallic laboratory (Organometallics) in an old rented gasoline station in Newburyport, a fire broke out.

Flames engulf the organometallics lab

After several futile attempts to extinguish it, I abandoned the effort. Neighbors reported seeing flames close to my back as I fled the burning building. Five years ago, I ended my career, again due to operator error, when there was a small but powerful explosion in the back lab of my New Hampshire premises. On this occasion, I escaped harm because I was answering nature’s call.

My interest in chemistry stemmed from a Gilbert Chemistry Set my parents gave me at a fairly early age. When I was a little older, I was able to purchase almost any chemical I wanted from a supply store in Lechmere Square. As a result, I experimented with most of the easily made explosives, but I never had much luck with black powder, and I never tried nitroglycerin.

I graduated from Somerville High School in 1942 and was admitted to the MIT class of 1946 without any examinations. WWII intervened, and over a period of three years, I worked in Guam as a power plant specialist on B-29s and also made ice cream for about 8 months at the EM’s Club. On returning to MIT, I graduated in Course V in the class of 1949.

Ed works on a B-29

I did my senior thesis for Professor Avery Morton with the plan of trying to settle the question of whether the Alfin catalyst, which gives a yield within 2 minutes of as much as 75% of polybutadiene based on the amount of 1,4-butadiene used, might contain a part of the catalyst. The resulting polymer has a molecular weight of several million and a micro structure very close to that of a radical initiated polymer. The catalyst is composed of allylsodium, sodium isopropoxide and sodium chloride­—which is necessary—although some chemists found that hard to believe. My work indicated that one allyl group is attached per polymer chain. Unsuccessful attempts had been made by one of Avery’s students to answer this question with coupling reactions, but with a MW of 1-2 million, this approach was hopeless, so I was going to try to use C14. I used C14 with the highest possible concentration to make allylsodium, converted it to the catalyst, and polymerized butadiene with it. The final radioactive concentration was so low that after numerous precipitations to remove any excess C14 compound, it required very long counts to get accurate values, but finally my results showed one allyl group per polymer chain. After getting a Masters degree in chemistry from Columbia University, I returned to MIT and entered graduate school. After approximately 8 months, I dropped out but continued to work for Avery Morton. My reasons for staying on to work in his lab were two-fold: (1) I had become very interested in organometallic chemistry and knew I wished to pursue a career in that area and (2) for many years, two entrepreneurial students in Morton’s lab, in their spare time, made and sold demonstration kits of the Alfin system to General Motors Previews of Progress Shows. Once Morton retired, I knew I would be well placed to take on the GM projects and that income alone would ensure I could live for a year.

An Alfn demonstration

After Morton discovered the Alfin catalyst, many chemists wanted samples to do physical studies. Being a classical organic chemist, Morton refused to send out samples until he had a pure polymer. This was a big mistake since Paul J. Flory got hold of an improperly prepared sample from one of the rubber companies and reported at a Rubber Reserve Meeting that, in spite of Morton’s claims, this was just a plain old sodium polymer. A real Alfin demonstration (see picture on right) shows that the Alfin polymer is clearly different than any polymer produced by sodium. Flory later admitted in a private meeting to Morton that he was incorrect, but Flory never corrected his error in public.

Fire or Hell!

Since so much work was being done on polymers in Morton’s Lab, I decided to take Professor Walter Stockmayer’s course on polymer chemistry, but I was the only one of Morton’s students who did. The late Professor Stockmayer (Stocky) while on a trip to France many years later, gave a talk to French chemists and pronounced my name as L’enfer, meaning fire or hell, which I thought was apt.

Around 1950, out of curiosity, I signed up for another of Stocky’s courses, this time in statistical mechanics. I had a few extra enrollment cards so in addition to my own card, I passed in one bearing Ludwig Boltzmann’s name. Some years later, when I was in Stocky’s MIT office, I saw the roll card displayed on his wall. I told him I was the perpetrator and we had a good laugh. About 15 years later I was in the area of Dartmouth so I stopped in to see Stocky in his office there. Once again, the card was on his wall. He told me that he’d had a few students say to him over the years, “I didn’t know Boltzmann was a student of yours.” I asked him if these were MIT or Dartmouth students, but he wouldn’t tell!

I got along with Morton very well despite his strong opinions which he held with great conviction, and with which I occasionally disagreed. He gave me almost total freedom in my research so long as it was in the area of organometallic chemistry. I authored 2 papers and co-authored 4 more with him, and I am fairly proud of the one I did on the structure of allylsodium, a very reactive compound and one that is not soluble in any solvent with which it won’t react. One day I started wondering what I might get if I made a nujol mull of it under a nitrogen blanket, so I put it between salt plates and ran an IR spectrum on it. The results were very interesting, showing a large downward shift from the normal double bond frequency to 1525 cm-1. I showed my findings to Professor Richard C. Lord who told me I had made a good start, but if I wanted to make assignments, I would have to make perdeuteroallysodium. With much help from Lord, we made assignments that indicated the terminal carbon atoms were at about 120 degrees and hugging the sodium atom. Not a big surprise!

I took IRs on quite a few more organomemetallic compounds and then it occurred to me to try the K salt of cyclooctratetraene. Again, there was a band with a large drop in the double bond region. Excited by this result, I rushed down to see Lord and got quite a surprise. Uncharacteristically agitated, he hurried to his blackboard and began drawing chair and boat sketches of cyclooctratetraene. He told me there was no way a COT ring was ever going to be planar due to a very high-energy barrier. A few years later, Professor Thomas Katz at Columbia University did some NMR work on the Li salt in solution that clearly showed that all 8 hydrogens were identical.

Some years later at an ACS mixer, my friend, Professor Dietmar Seyferth, was in the act of introducing me to Professor E.O. Wilson. While Seyferth spoke, I noticed Wilson glancing down at my nametag. In mid-sentence he interrupted Dietmar by saying, “that of course, he knew my name because I had published…” I was admittedly pleased that he was familiar with my work, but Dietmar, in his inimitable way, quickly burst my balloon by remarking, “Professor Wilson is very familiar with the older literature.” Well, that was a nice quip, but of course it wasn’t in the same league as a remark he made in 2002. This time it was at the rededication of the newly refurbished chemistry Building 18. Seyferth was invited to give an oral history of the department, which he did to great aplomb to a packed audience in 10-250. When it came time to talk about the late Professor Al Cotton, he remarked, “Al is still waiting for the CALL.”

Now back to my charmed life. After destroying my rented gasoline station, I was no longer welcome in Newburyport. Fortunately, two chemists I knew offered me space in Gloucester where I worked for a few months. Out of the blue, I got a call from a man in Ipswich whose wife and partner had both died in a double suicide, a double murder, or a murder and suicide, and he promised to erect a good building for me that I could let as soon as his wife’s estate was settled! In the meantime, he offered me the use of an unheated garage, and, as the weather began to get cooler with no sign of the promised building, I set out to find alternative premises. Soon, I found an old colonial in Hampstead, NH, with a small building at a reasonably (safe) distance from the house where I installed a 200 pound automatic CO2 system. A few years later, I needed more space so I rented some from Dr. Henry Hill (the first African American PhD student at MIT) who operated his industrial chemistry company in Haverhill, MA. At this time I was collaborating with a former student of Morton’s, Dr. I. Hechenbliekner, known as Heck. Heck had almost 100 patents to his name.

My final move was to buy 5 acres in East Hampstead, NH, in 1973 where I set up my home and my lab. Some years after moving, Heck told me he had 500 pounds of impure Me2SnCl2 that he was prepared to sell to me at a very low price. The material contained small amounts of Me3SnCl, a very powerful sternutater which most likely lowered the MP of the product a bit. Heck tried to send the material by air, but the product was not quite solid and some of it leaked onto the fuselage and shipment was refused. Heck told me he came close to buying the plane! I drove to West Virginia, loaded as much of the product as I could in my trunk and the rest on my back seat. The odor was such that I had to keep all the windows open for the trip. It was worth it. Me2SnCl2 was a great material for making Me4Sn using TMA, and I used it for many years.

When I finally closed the lab after the aforementioned explosion, I found a home for much of my surviving glassware in the lab of Assistant Professor Mircea Dinca in the chemistry department at MIT. It’s a fitting place for it to end up, and Mircea was really delighted to receive it.

Despite nearly losing my life twice in my lab, I made a very good living from chemistry, and I credit my interesting career to MIT. As such, I have arranged a planned gift to the department to use for graduate fellowships. I can’t think of a better way to give back.